Allyl bromide → HCID 58562838, compound

HRID 1896807Notes

Reaction equation

HRID 1896807 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([OH:15])[CH2:12][CH:13]=[CH2:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20]>>[CH2:20]([O:15][CH:11]([CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH2:12][CH:13]=[CH2:14])[CH:19]=[CH2:18]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 58562619HCID 58562619, compound

Product 1

HCID 58562838HCID 58562838, compound

Procedure

A solution of 1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-ol (436 mg, 2.05 mmol), prepared in the previous step, was added to a suspension of sodium hydride (104 mg, 4.12 mmol, 95%) dropwise at 0° C. under argon. After the complete addition, the reaction mixture was allowed to reach room temperature and stirred 1 hour. Allyl bromide (0.35 mL, 4.05 mmol) was added dropwise and the mixture stirred overnight at room temperature. It was poured onto ice cooled saturated NaHCO3 solution. After extraction with ether, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, DCM) to afford the product.

Workup

  1. additionAfter the complete addition
  2. customto reach room temperature
  3. stirringthe mixture stirred overnight at room temperature
  4. additionIt was poured onto ice cooled saturated NaHCO3 solution
  5. extractionAfter extraction with ether
  6. concentrationthe organic layer was concentrated in vacuo
  7. customthe residue purified by flash chromatography (silica gel, DCM)
  8. customto afford the product

Sources & evidence

ORD record
ord-f857669ed0da401da343d87564e47bd1
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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